Various ligands and catalysts are known for hydrocarbon and carbon monoxide conversion reactions. For example, rhodium catalysts containing triaryl phosphine ligands have been extensively used for hydroformylation reactions. Likewise, cobalt hydroformylation catalysis has been widely used commercially, but the addition of phosphine ligands has proven of only minor value in such reactions.
Transition metal complexes of both triphenylphosphine and trialkyl phosphine have been widely studied as catalysts for hydroformylation, hydrogenation, etc. For their application in reactions of carbon monoxide, particularly carbonylations, see the monograph of Juergen Falbe, "Carbon Monoxide in Organic Synthesis," Springer Verlag, New York, 1970. Also, general discussion of catalysis of reactions of carbon monoxide is included in "Homogeneous Catalysis Involving Carbon Monoxide" Catalysis, Vol. I, Specialist Periodical Reports V, The Chemical Society, Burlington House, London, 1977 by Davidson, et al. In the area of rhodium catalyzed hydroformylations of alpha-olefins, homogeneous catalyst systems employing triaryl phosphine and other trivalent phosphorus compounds in complex with rhodium plus excess phosphine ligand were described by R. L. Pruett and J. A. Smith in U.S. Pat. No. 3,527,809.
Certain transition metal complexes containing phosphines covalently anchored to polymeric substrates have also been disclosed as heterogeneous catalyst systems. Such polymer-anchored complexes were reviewed by C. C. Leznoff in Vol. III, pp. 65-85, of the Chemical Society Review in 1974. The polymer-anchored rhodium hydroformylation catalysts were also discussed in detail in the Journal of Organometallic Chemistry, Vol. 134, pp. 85-94, in 1977 by W. H. Lang, A. T. Jurezicz, W. O. Haag, D. D. Whitehurst and L. D. Rollmann. Other complexes covalently anchored to inorganic solids, such as silica, were disclosed in a number of U.S. patents such as U.S. Pat. No. 3,726,809 by K. G. Allum, S. McKenzie and R. C. Pitkethly and U.S. Pat. No. 4,151,114 by A. A. Oswald and L. L. Murrell.
Oswald in U.S. Pat. Nos. 4,136,103 and 3,929,849 discloses tetraakylphosphonium aluminosilicates and complexes thereof with group VIII transition metals, e.g., rhodium. There is no suggestion in these patents of using such catalyst in any hydrocarbon and carbon monoxide conversion processes.
Still other patents have described bis-phosphine compounds as complexes for rhodium. For example, Booth in U.S. Pat. Nos. 3,965,192 and 3,560,539 discloses ethylene bis-(diphenylphosphine) as a ligand for rhodium complexes.
McVicker in U.S. Pat. Nos. 3,939,188 and 3,946,082 discloses processes for preparing oxygenated products such as aldehydes and suggests as catalysts for his process zero valent rhodium complexes with various ligands thereon. As ligands for such complexes, McVicker suggests, for example, phosphine ligands with various substituents selected from a long list of possibilities among which are included halides such as fluoride, alkyl, alkoxy, cycloalkyl, cycloalkoxy, phenyl, phenyl substituted with halide, phenyl substituted with cycloalkyl, phenyl substituted with alkoxy, oxyphenyl, oxyphenyl substituted with alkyl, oxyphenyl substituted with cycloalkyl, oxyphenyl substituted with halide and oxyphenyl substituted with cycloalkoxy.
Kawse in U.S. Pat. No. 4,013,700 discloses a process for the manufacture of polyhydric alcohols and their ether and ester derivatives by reacting oxides of carbon and hydrogen in the presence of small amounts of a quaternary phosphonium cation and a rhodium carbonyl complex. Exemplary quaternary phosphonium cations for the Kawse process are described in Column 4, lines 8-41 of the patent.
Some of the latest advancements in Fischer-Tropsch and water-gas shift reactions are disclosed in "Advances in Fischer-Tropsch Chemistry" by M. E. Dry in Ind. Eng. Chem., Prod. Res. Dev., Vol. 15, No. 4, 1976; "Reductions With Carbon Monoxide and Water in Place of Hydrogen. 1. Hydroformylation Reaction and Water-Gas Shift" by H. C. Kang, et al in Journal of the American Chemical Society, Vol. 99, pp. 8323-8324 (1977); and "Coal Research Shifts to Soluble Catalysts" in Chemical Week, Apr. 19, 1978, pp. 63 and 65. Advances in the use of silicate clusters are discussed in "New Silicate Has Cluster of Uses," Chemical Week, Mar. 7, 1979, pp. 37 and 38. Various aspects of the support of metal complex catalysts on metal oxide supports as well as the use of such materials in photo reactions are discussed in "Chemical Modification of a Titanium(IV) Oxide Electrode to Give Stable Dye Sensitisation Without a Supersensitiser" by S. Anderson, et al in Nature, Vol. 280, Aug. 16, 1979 and "Photo-electrochemical Conversion of Optical Energy to Electricity and Fuels," by M. S. Wrighton in Accounts of Chemical Research, Vol. 12, No. 9, pp. 303-310 (September, 1979). Other aspects of Fischer-Tropsch synthesis and similar reactions are discussed in "Carbon Monoxide-Hydrogen Reactions," by H. Pichler, Kirk Othmer's Encyclopedia of Chemical Technology (Second Edition), Vol. 4, pp. 446-489 (1964).